CN1165145A - 制备亚膦酸单烷基酯的方法 - Google Patents
制备亚膦酸单烷基酯的方法 Download PDFInfo
- Publication number
- CN1165145A CN1165145A CN97102420A CN97102420A CN1165145A CN 1165145 A CN1165145 A CN 1165145A CN 97102420 A CN97102420 A CN 97102420A CN 97102420 A CN97102420 A CN 97102420A CN 1165145 A CN1165145 A CN 1165145A
- Authority
- CN
- China
- Prior art keywords
- phosphine
- dichloro
- formula
- described method
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 16
- LWNLXVXSCCLRRZ-UHFFFAOYSA-N dichlorophosphane Chemical class ClPCl LWNLXVXSCCLRRZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011541 reaction mixture Substances 0.000 claims abstract description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000460 chlorine Substances 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000002500 ions Chemical class 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- PTKUMHCGCMXGAD-UHFFFAOYSA-N 3-chloropropylphosphane Chemical class PCCCCl PTKUMHCGCMXGAD-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- IKNPUBSFLQLSLS-UHFFFAOYSA-N butyl(dichloro)phosphane Chemical compound CCCCP(Cl)Cl IKNPUBSFLQLSLS-UHFFFAOYSA-N 0.000 claims description 2
- -1 chloro-4-dimethylaminophenyl phosphines Chemical class 0.000 claims description 2
- MJEQIIGWDHUZJW-UHFFFAOYSA-N dichloro(cyclohexyl)phosphane Chemical compound ClP(Cl)C1CCCCC1 MJEQIIGWDHUZJW-UHFFFAOYSA-N 0.000 claims description 2
- JHNJGLVSPIMBLD-UHFFFAOYSA-N dichloro(ethyl)phosphane Chemical compound CCP(Cl)Cl JHNJGLVSPIMBLD-UHFFFAOYSA-N 0.000 claims description 2
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 238000013019 agitation Methods 0.000 description 7
- 238000003828 vacuum filtration Methods 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- AWYDVYYDVPFOMZ-UHFFFAOYSA-N dichloromethylphosphane Chemical class PC(Cl)Cl AWYDVYYDVPFOMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- GFMYEVPBEJFZHH-UHFFFAOYSA-N CP(O)(O)O Chemical compound CP(O)(O)O GFMYEVPBEJFZHH-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 238000006298 dechlorination reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- HAEFDDOAYBQRGK-UHFFFAOYSA-N 2-methylpropylphosphonic acid Chemical class CC(C)CP(O)(O)=O HAEFDDOAYBQRGK-UHFFFAOYSA-N 0.000 description 1
- QCIFWXKPYVQMGY-UHFFFAOYSA-N COP(O)(O)C Chemical class COP(O)(O)C QCIFWXKPYVQMGY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KIOOPXXIFXEVLQ-UHFFFAOYSA-N Cl[P]Cl Chemical compound Cl[P]Cl KIOOPXXIFXEVLQ-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- DWZJMJGRGQVJBN-UHFFFAOYSA-N chloro(propan-2-yl)phosphane Chemical class CC(C)PCl DWZJMJGRGQVJBN-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- PUDFIJVVIPLMQS-UHFFFAOYSA-N dichloro(2-methylpropyl)phosphane Chemical class CC(C)CP(Cl)Cl PUDFIJVVIPLMQS-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19604195A DE19604195C1 (de) | 1996-02-06 | 1996-02-06 | Verfahren zur Herstellung von Phosphonigsäuremonoalkylestern |
| DE19604195.3 | 1996-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1165145A true CN1165145A (zh) | 1997-11-19 |
Family
ID=7784613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97102420A Pending CN1165145A (zh) | 1996-02-06 | 1997-02-03 | 制备亚膦酸单烷基酯的方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5734072A (enExample) |
| EP (1) | EP0789027A1 (enExample) |
| JP (1) | JPH09309891A (enExample) |
| CN (1) | CN1165145A (enExample) |
| BR (1) | BR9700883A (enExample) |
| DE (1) | DE19604195C1 (enExample) |
| IN (1) | IN182568B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101830926A (zh) * | 2010-05-04 | 2010-09-15 | 云梦县江山新材料有限公司 | 二烷基次膦酸金属盐及其阻燃剂的合成工艺 |
| CN103435643A (zh) * | 2013-08-08 | 2013-12-11 | 清远市普塞呋磷化学有限公司 | 一种单羟基二烷基次膦酸金属盐阻燃剂的制备方法 |
| CN101720329B (zh) * | 2007-07-13 | 2014-08-06 | 科莱恩金融(Bvi)有限公司 | 烷基亚膦酸，烷基亚膦酸盐和烷基亚膦酸酯，它们的制备方法及它们的用途 |
| CN107021981A (zh) * | 2017-04-11 | 2017-08-08 | 四川福思达生物技术开发有限责任公司 | 一种甲基乙基次磷酸铝的制备方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2311950A1 (en) * | 1997-11-28 | 1999-06-10 | Clariant Gmbh | Process for alkylating elemental phosphorus |
| DE19828861C1 (de) * | 1998-06-29 | 1999-12-02 | Clariant Gmbh | Verfahren zur Herstellung von Phosphonigsäureestern und deren Verwendung |
| DE10360771A1 (de) * | 2003-12-23 | 2005-07-28 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von dreiwertigen Organophosphor-Verbindungen |
| JP2012520365A (ja) | 2009-03-13 | 2012-09-06 | ビーエーエスエフ ソシエタス・ヨーロピア | ポリエステル及びポリアミドの安定化されたブレンド |
| CN102348762A (zh) | 2009-03-13 | 2012-02-08 | 巴斯夫欧洲公司 | 聚酯和聚酰胺的稳定化共混物 |
| NL2013088B1 (en) | 2014-06-30 | 2016-07-11 | Knowfort Holding B V | A process for preparation of a composite layer or a laminate, and product obtained therewith. |
| DE102015218442A1 (de) | 2015-09-25 | 2017-03-30 | Robert Bosch Gmbh | Biosensor und Verfahren zum Nachweis von Keimen |
| TW201840578A (zh) | 2017-02-22 | 2018-11-16 | 以色列商亞當阿甘公司 | 製備甲基膦酸丁基酯的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2903475A (en) * | 1956-04-16 | 1959-09-08 | Virginia Carolina Chem Corp | Production of esters of phosphonous and phosphinous acids |
| GB853982A (en) * | 1956-04-16 | 1960-11-16 | Virginia Carolina Chem Corp | Production of alkyl, aryl and aralkyl esters of acids of trivalent phosphorus |
| FR2624286A1 (fr) * | 1987-12-03 | 1989-06-09 | Automatismes Controles Electro | Compteur horaire pour moteurs a explosions |
| GB8728483D0 (en) * | 1987-12-04 | 1988-01-13 | Ciba Geigy Ag | Chemical compounds |
| GB8912814D0 (en) * | 1989-06-03 | 1989-07-19 | Ciba Geigy Ag | P-substituted propane-phospinic acid compounds |
| US5190934A (en) * | 1989-06-03 | 1993-03-02 | Ciba-Geigy Corporation | P-subsituted propane-phosphinic acid compounds |
-
1996
- 1996-02-06 DE DE19604195A patent/DE19604195C1/de not_active Expired - Fee Related
-
1997
- 1997-01-17 IN IN92CA1997 patent/IN182568B/en unknown
- 1997-01-22 EP EP97100943A patent/EP0789027A1/de not_active Withdrawn
- 1997-02-03 CN CN97102420A patent/CN1165145A/zh active Pending
- 1997-02-05 JP JP9022985A patent/JPH09309891A/ja not_active Withdrawn
- 1997-02-05 US US08/794,439 patent/US5734072A/en not_active Expired - Fee Related
- 1997-02-05 BR BR9700883A patent/BR9700883A/pt active Search and Examination
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101720329B (zh) * | 2007-07-13 | 2014-08-06 | 科莱恩金融(Bvi)有限公司 | 烷基亚膦酸，烷基亚膦酸盐和烷基亚膦酸酯，它们的制备方法及它们的用途 |
| CN101830926A (zh) * | 2010-05-04 | 2010-09-15 | 云梦县江山新材料有限公司 | 二烷基次膦酸金属盐及其阻燃剂的合成工艺 |
| CN101830926B (zh) * | 2010-05-04 | 2013-04-17 | 洪湖市一泰科技有限公司 | 二烷基次膦酸金属盐及其阻燃剂的合成工艺 |
| CN103435643A (zh) * | 2013-08-08 | 2013-12-11 | 清远市普塞呋磷化学有限公司 | 一种单羟基二烷基次膦酸金属盐阻燃剂的制备方法 |
| CN107021981A (zh) * | 2017-04-11 | 2017-08-08 | 四川福思达生物技术开发有限责任公司 | 一种甲基乙基次磷酸铝的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US5734072A (en) | 1998-03-31 |
| DE19604195C1 (de) | 1997-04-17 |
| JPH09309891A (ja) | 1997-12-02 |
| BR9700883A (pt) | 1998-10-27 |
| IN182568B (enExample) | 1999-05-08 |
| EP0789027A1 (de) | 1997-08-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |